Bicarbonate Ion → 2768-53-8

HRID 1450728Notes

Reaction equation

HRID 1450728 reaction equation
[NH:1]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C@H:2]([C:4]([NH:6][C@H:7]([C:15]([O:17]C)=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:3].O[Li].O.N(C(OCC1C=CC=CC=1)=O)[C@H](C(N[C@H](C(NCC(OCC1C=CC=CC=1)=O)=O)CC1C=CC=CC=1)=O)C.C(=O)(O)[O-]>C1COCC1.O>[NH:1]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C@H:2]([C:4]([NH:6][C@H:7]([C:15]([OH:17])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:3]

Participants

7

Reactant 4

HCID 769Bicarbonate IonHCID 168937Lithium hydroxide, monohydrateHCID 6999129HCID 6999129, compoundHCID 101919896HCID 101919896, compound

Product 1

HCID 69991262768-53-8

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To methyl ester 21 (1.64 g, 4.27 mmol) dissolved in 25 mL of THF and cooled to 0° C. was added LiOH.H2O (0.25 g, 140 mol %) dissolved in 8 mL of water. The resulting solution was cooled to 0° C., added to the THF solution of 27, stirred at 0° C. for 0.5 h, then poured into 50 mL of saturated aqueous bicarbonate. The basic mixture was then extracted with 50 mL of ether which was discarded. The water layer was acidified with 1N HCl to pH 2 and extracted with 2×100 mL of ether. The organic extracts were combined, dried, and evaporated to give a thick white foam, which was crystallized from ether/hexane affording 1.53 g, 97% of 11 as a white powder; mp 126°-127° C.; [α]25D +39.8° (c 2.1, CHCl3); 1H NMR δ 11.5-11.1 (br s, 1H), 7.40-7.10 (m, 10H), 6.80 (d, 1H, J=5), 5.49 (d, 1H, J=4), 5.07 (s, 2H), 4.49-4.46 (m, 1H), 4.25-4.23 (m, 1H), 3.18 (dd, 1H, J=14, 5.5), 3.03 (dd, 1H, J=14, 6.5), 1.28 (d, 3H, J=7). Anal. Calcd for C24H22N3O5 : C, 64.8; H, 6.0,; N, 7.6. Found: C, 64.8; H, 6.0; N, 7.4.

Workup

  1. temperatureThe resulting solution was cooled to 0° C.
  2. extractionThe basic mixture was then extracted with 50 mL of ether which
  3. extractionextracted with 2×100 mL of ether
  4. customdried
  5. customevaporated
  6. customto give a thick white foam, which
  7. customwas crystallized from ether/hexane affording 1.53 g, 97% of 11 as a white powder

Sources & evidence

ORD record
ord-08004da54ba64a2fbf00fabf8853b558
Source dataset
uspto-grants-1997_02
Patent number
US05602264

Reaction notes

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